After hiring 39 employees offshore over the past four years, I thought I’d share some of the mistakes and lessons our team has picked up along the way. In talking with a bunch of AI agency founders recently, I’ve noticed that most of them can’t scale because they’re buried in automation work, and they put off making their first hire because it feels daunting. Hopefully, these six lessons make that step a little easier. START WITH A CONTRACT A lot of problems creep in if you skip this step. The contract doesn’t need to be filled with legal jargon. Just something both sides can point back to if questions come up, outlining expectations around working hours, pay, responsibilities, and a paid trial period. Happy to share a template. OUTLINE INITIAL PROJECTS To start with, choose a small project that can be completed within 1-2 weeks. This gives both you and your automation assistant a chance to go through a full work cycle quickly and align on expectations and workflows. CREATE AN ONBOARDING CHECKLIST Spend some time thinking through what you want the onboarding experience to be like, and define the steps in a checklist. This should include: Setting up necessary accounts, ensuring tool access, and clarifying weekly tasks and goals for the first month. OVER-COMMUNICATE AT THE START Daily check-ins might feel like too much, but they will save you from weeks of misalignment. You’ll review what your assistant accomplished the previous day, discuss what they plan to work on today, and address any blockers they might be facing. After the first two weeks, you can transition to async check-ins. HIRE FOR TRAITS, NOT JUST SKILLS New AI and automation tools are being released on a weekly basis. You don’t need someone who is an expert at everything. You need somebody who is curious, proactive, communicates well, and can learn things quickly. HAVE A REQUIREMENTS DOC FOR YOUR PROJECTS The best ways to save yourself time (and respect your assistant’s time) is to put together a lightweight PRD (Product Requirements Document). At a minimum, outline the scope of the project, the KPIs or success metrics you care about, and the tools or resources they’ll need access to.

🚀 Landed my first AI Automation client – we’re streamlining their lead generation so they can focus on closing deals, not chasing leads. This is proof that AI = growth engine. 🔥 A special thanks to @Nate Herk 🙌 for the inspiration and guidance—your content and insights have been a real game-changer in this journey. 👉 If AI could automate one task in your business, what would you choose?